Skip to main content
U.S. Department of Energy
Office of Scientific and Technical Information

Lignin monomer conversion into biolubricant base oils

Journal Article · · Green Chemistry
DOI:https://doi.org/10.1039/d1gc03350f· OSTI ID:1978795
 [1];  [2];  [3];  [2]
  1. Univ. of Delaware, Newark, DE (United States). Catalysis Center for Energy Innovation (CCEI); OSTI
  2. Univ. of Delaware, Newark, DE (United States). Catalysis Center for Energy Innovation (CCEI)
  3. Univ. of Delaware, Newark, DE (United States). Catalysis Center for Energy Innovation (CCEI); Tianjin Univ. (China)

Despite progress in the depolymerization of lignin, only a few studies convert the obtained monomers to value-added products. Here we introduce a strategy to synthesize branched benzene lubricant (BBL) and branched cyclic lubricant (BCL) base oils from lignin-derived monomers and aldehyde. We perform carbon–carbon coupling via Brønsted acid-catalyzed hydroxyalkylation/alkylation (HAA) then hydrodeoxygenation (HDO). Optimum HAA reaction conditions achieve up to 90% guaiacol conversion and an HAA product containing 76% BBL and 24% enal condensation product over a P-SiO2 catalyst. Subsequent HDO of HAA products over an Ir-ReOx/SiO2 catalyst produces a lubricant-ranged mixture of BCL (C24) up to yield (82%) and small fractions of dodecyl cyclohexane and C10 and C15 carbons alkanes. The kinematic viscosity, viscosity index, and Noack volatility of these base oils are comparable to commercial petroleum-derived poly α-olefin Group IV and refrigerant base oils. In conclusion, this approach provides a sustainable pathway for replacing petroleum-derived base oils.

Research Organization:
Univ. of Delaware, Newark, DE (United States); Energy Frontier Research Centers (EFRC) (United States). Catalysis Center for Energy Innovation (CCEI)
Sponsoring Organization:
USDOE Office of Science (SC), Basic Energy Sciences (BES)
Grant/Contract Number:
SC0001004
OSTI ID:
1978795
Alternate ID(s):
OSTI ID: 1832650
Journal Information:
Green Chemistry, Journal Name: Green Chemistry Journal Issue: 24 Vol. 23; ISSN 1463-9262
Publisher:
Royal Society of ChemistryCopyright Statement
Country of Publication:
United States
Language:
English

References (41)

C−O Hydrogenolysis of Tetrahydrofurfuryl Alcohol to 1,5-Pentanediol Over Bi-functional Nickel-Tungsten Catalysts journal September 2018
Synthesis of Renewable Bisphenols from Creosol journal December 2011
Synthesis of High-Quality Diesel with Furfural and 2-Methylfuran from Hemicellulose journal August 2012
Zeolites as sustainable catalysts for the selective synthesis of renewable bisphenols from lignin-derived monomers journal April 2017
Selective Hydrodeoxygenation of Vegetable Oils and Waste Cooking Oils to Green Diesel Using a Silica-Supported Ir-ReO x Bimetallic Catalyst journal April 2018
Branched Bio‐Lubricant Base Oil Production through Aldol Condensation journal September 2019
Chemistry of delignification journal December 1985
A Study of Tetrahydrofurfuryl Alcohol to 1,5-Pentanediol Over Pt–WOx/C journal February 2018
Solubility and viscosity of refrigerant/lubricant mixtures: hydrofluorocarbon/alkylbenzene systems journal December 2002
Hydrogenation of carboxylic acids to the corresponding aldehydes journal November 2001
Kinetic study and reaction mechanism of the hydroxyalkylation of aromatic compounds over H-BEA zeolites journal March 2001
A review on the catalytic hydrodeoxygenation of lignin-derived phenolic compounds and the conversion of raw lignin to hydrocarbon liquid fuels journal January 2020
Green solvents-based fractionation process for kraft lignin with controlled dispersity and molecular weight journal November 2019
Production of 1,5-pentanediol from biomass via furfural and tetrahydrofurfuryl alcohol journal November 2012
A concise review of current lignin production, applications, products and their environmental impact journal November 2019
Flowthrough Reductive Catalytic Fractionation of Biomass journal November 2017
Global lignin supply overview and kraft lignin potential as an alternative for petroleum-based polymers journal May 2020
A Mechanistic Study of Polyol Hydrodeoxygenation over a Bifunctional Pt-WO x /TiO 2 Catalyst journal October 2020
Synthesis of 1,6-Hexanediol from Cellulose Derived Tetrahydrofuran-Dimethanol with Pt-WO x /TiO 2 Catalysts journal January 2018
Mechanistic Study of the Direct Hydrodeoxygenation of m -Cresol over WO x -Decorated Pt/C Catalysts journal July 2018
From Tree to Tape: Direct Synthesis of Pressure Sensitive Adhesives from Depolymerized Raw Lignocellulosic Biomass journal May 2018
From Wood to Tetrahydro-2-benzazepines in Three Waste-Free Steps: Modular Synthesis of Biologically Active Lignin-Derived Scaffolds journal October 2019
100th Anniversary of Macromolecular Science Viewpoint: Polymers from Lignocellulosic Biomass. Current Challenges and Future Opportunities journal March 2020
Selective Synthesis of 4,4′-Dimethylbiphenyl from 2-Methylfuran journal February 2021
Renewable Epoxy Networks Derived from Lignin-Based Monomers: Effect of Cross-Linking Density journal July 2016
Chemical Bonding and Aromaticity in Furan, Pyrrole, and Thiophene: A Magnetic Shielding Study journal August 2013
Density Functional Theory Study of Mixed Aldol Condensation Catalyzed by Acidic Zeolites HZSM-5 and HY journal August 2014
Stabilization strategies in biomass depolymerization using chemical functionalization journal May 2020
Reductive lignocellulose fractionation into soluble lignin-derived phenolic monomers and dimers and processable carbohydrate pulps journal January 2015
Synthesis of 1,6-hexanediol from HMF over double-layered catalysts of Pd/SiO 2 + Ir–ReO x /SiO 2 in a fixed-bed reactor journal January 2016
Production of renewable lubricants via self-condensation of methyl ketones journal January 2016
Catalytic production of renewable lubricant base oils from bio-based 2-alkylfurans and enals journal January 2019
Thiol-promoted catalytic synthesis of high-performance furan-containing lubricant base oils from biomass derived 2-alkylfurans and ketones journal January 2020
Reductive catalytic fractionation of agricultural residue and energy crop lignin and application of lignin oil in antimicrobials journal January 2020
One-step lignocellulose depolymerization and saccharification to high sugar yield and less condensed isolated lignin journal January 2021
Chemoselective hydrogenolysis of tetrahydrofurfuryl alcohol to 1,5-pentanediol journal January 2009
Formaldehyde stabilization facilitates lignin monomer production during biomass depolymerization journal October 2016
A sustainable wood biorefinery for low–carbon footprint chemicals production journal February 2020
Catalytic Hydrodeoxygenation of Lignin-Derived Feedstock Into Arenes and Phenolics journal September 2020
Efficient Fractionation of Lignin- and Ash-Rich Agricultural Residues Following Treatment With a Low-Cost Protic Ionic Liquid journal April 2019
Quantification and Variability Analysis of Lignin Optical Properties for Colour-Dependent Industrial Applications journal February 2018